5-alkyl-7-alkylcarbonate-isoflavone ester and related method

Abstract

A compound is provided for increasing the concentration of a parent isoflavone in a subject in vivo. The parent isoflavone has a skeletal structure including a 5 position and a 7 position, a 5 alkyl group, and a 7-hydroxy group with a 7-hydroxy oxygen appended to the 7 position and a 7-hydroxy hydrogen appended to the 7-hydroxy oxygen. The compound includes a substrate having the skeletal structure of the parent isoflavone, with a 5 position and a 7 position corresponding to the 5 and 7 positions respectively of the parent isoflavone. An alkyl group is appended to the 5 position. A promoiety is appended to the 7-hydroxy oxygen of the substrate as a substitute for the 7-hydroxy hydrogen of the parent isoflavone the promoiety and the 7-hydroxy oxygen establishing an alkylcarbonate ester. A related method also is provided.

1. A method for increasing the concentration of a parent isoflavone in a subject in vivo, the parent isoflavone having a skeletal structure including a 5 position and a 7 position and the parent isoflavone further having a 5 alkyl group and a 7-hydroxy group comprising a 7-hydroxy oxygen appended to the 7 position and a 7-hydroxy hydrogen appended to the 7-hydroxy oxygen, the method comprising:
 administering to the subject a compound comprising formula I, and 
 wherein the compound is converted in vivo into the parent isoflavone, 
 wherein formula I is represented by 
 
       
         
           
           
               
               
           
         
         wherein 
         R 1  consists of a member selected from the group consisting of a straight-chain, branched, and cyclic alkyl; 
         R 2  consists of a member selected from the group consisting of a straight-chain, branched, and cyclic alkyl; 
         R 3  and R 4  are the same or different, and selected from the group consisting of hydrogen, alkyl, hydroxy, and alkyoxy; and 
         R 5  consists of a member selected from the group consisting of hydrogen and an alkyl. 
       
     
     
       2. A method as set forth in  claim 1 , wherein R 1  has a maximum of 12 carbon atoms. 
     
     
       3. A method as set forth in  claim 1 , wherein the alkylcarbonate ester consists of a member selected from the group consisting of methyl carbonate, ethyl carbonate, propyl carbonate, isopropyl carbonate, butyl carbonate, isobutyl carbonate, t-butyl carbonate, valeryl carbonate, hexyl carbonate, heptyl carbonate, octyl carbonate, nonyl carbonate, decyl carbonate, undecyl carbonate, dodecyl carbonate, cyclopentyl methyl carbonate, cyclopentylpropyl carbonate, cyclohexyl methyl carbonate, and cyclohexylpropyl carbonate. 
     
     
       4. A method as set forth in  claim 1 , wherein the alkylcarbonate ester consists of ethyl carbonate. 
     
     
       5. A method as set forth in  claim 1 , wherein R 2  consists of methyl. 
     
     
       6. A method for increasing the concentration of a parent isoflavone in a subject in vivo, the parent isoflavone having a skeletal structure including a 5 position and a 7 position and the parent isoflavone further having a 5 alkyl group and a 7-hydroxy group comprising a 7-hydroxy oxygen appended to the 7 position and a 7-hydroxy hydrogen appended to the 7-hydroxy oxygen, the method comprising:
 administering to the subject a compound comprising formula I, and 
 wherein the compound is converted in vivo into the parent isoflavone, 
 wherein formula I is represented by 
 
       
         
           
           
               
               
           
         
         wherein 
         R 1  consists of a member selected from the group consisting of a straight-chain, branched, and cyclic alkyl; and 
         R 2  consists of a member selected from the group consisting of a straight-chain, branched, and cyclic alkyl. 
       
     
     
       7. A method as set forth in  claim 6 , wherein R 1  has a maximum of 12 carbon atoms. 
     
     
       8. A method as set forth in  claim 6 , wherein the alkylcarbonate ester consists of a member selected from the group consisting of methyl carbonate, ethyl carbonate, propyl carbonate, isopropyl carbonate, butyl carbonate, isobutyl carbonate, t-butyl carbonate, valeryl carbonate, hexyl carbonate, heptyl carbonate, octyl carbonate, nonyl carbonate, decyl carbonate, undecyl carbonate, dodecyl carbonate, cyclopentyl methyl carbonate, cyclopentylpropyl carbonate, cyclohexyl methyl carbonate, and cyclohexylpropyl carbonate. 
     
     
       9. A method as set forth in  claim 6 , wherein the alkylcarbonate ester consists of ethyl carbonate. 
     
     
       10. A method as set forth in  claim 6 , wherein R 2  consists of methyl. 
     
     
       11. A method for increasing the concentration of a parent isoflavone in a subject in vivo, the parent isoflavone having a skeletal structure including a 5 position and a 7 position and the parent isoflavone further having a 5 alkyl group and a 7-hydroxy group comprising a 7-hydroxy oxygen appended to the 7 position and a 7-hydroxy hydrogen appended to the 7-hydroxy oxygen, the method comprising:
 administering to the subject a compound comprising a substrate and a promoiety, the substrate having the skeletal structure of the parent isoflavone, the substrate comprising a 5 position and a 7 position corresponding to the 5 and 7 positions respectively of the parent isoflavone, the 5 position having an alkyl group appended thereto, the promoiety being appended to the 7-hydroxy oxygen of the substrate as a substitute for the 7-hydroxy hydrogen of the parent isoflavone, the promoiety and the 7-hydroxy oxygen establishing an alkylcarbonate ester 
 wherein the compound is converted in vivo into the parent isoflavone. 
 
     
     
       12. A method as set forth in  claim 11 , wherein the promoiety has a maximum of 12 carbon atoms. 
     
     
       13. A method as set forth in  claim 11 , wherein the alkylcarbonate ester consists of a member selected from the group consisting of methyl carbonate, ethyl carbonate, propyl carbonate, isopropyl carbonate, butyl carbonate, isobutyl carbonate, t-butyl carbonate, valeryl carbonate, hexyl carbonate, heptyl carbonate, octyl carbonate, nonyl carbonate, decyl carbonate, undecyl carbonate, dodecyl carbonate, cyclopentyl methyl carbonate, cyclopentylpropyl carbonate, cyclohexyl methyl carbonate, and cyclohexylpropyl carbonate. 
     
     
       14. A method as set forth in  claim 11 , wherein the alkylcarbonate ester consists of ethyl carbonate. 
     
     
       15. A method as set forth in  claim 11 , wherein the alkyl group appended to the 5 position is methyl. 
     
     
       16. A method as set forth in  claim 15 , wherein the promoiety has a maximum of 12 carbon atoms. 
     
     
       17. A method as set forth in  claim 15 , wherein the alkylcarbonate ester consists of a member selected from the group consisting of methyl carbonate, ethyl carbonate, propyl carbonate, isopropyl carbonate, butyl carbonate, isobutyl carbonate, t-butyl carbonate, valeryl carbonate, hexyl carbonate, heptyl carbonate, octyl carbonate, nonyl carbonate, decyl carbonate, undecyl carbonate, dodecyl carbonate, cyclopentyl methyl carbonate, cyclopentylpropyl carbonate, cyclohexyl methyl carbonate, and cyclohexylpropyl carbonate. 
     
     
       18. A method as set forth in  claim 15 , wherein the alkylcarbonate ester consists of ethyl carbonate.